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Diethyl Ether → 4-Amino-6-benzyloxy-7-methoxy-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinazoline

HRID 1004002
Notes
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Reaction equation

HRID 1004002 reaction equation
Cl.[N:2]1([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[NH2:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:36][CH3:37])=[C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:26]=2)[N:21]=[C:20](Cl)[N:19]=1.C(N(CC)CC)C.C(OCC)C>C(O)CCC>[NH2:17][C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:36][CH3:37])=[C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:26]=2)[N:21]=[C:20]([N:13]2[CH2:14][CH2:15][CH2:16][N:10]([C:8]([N:2]3[CH2:3][CH2:4][O:5][CH2:6][CH2:7]3)=[O:9])[CH2:11][CH2:12]2)[N:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 109799944-Amino-6-benzyloxy-2-chloro-7-methoxyquinazolineHCID 227070621-(4-Morpholinecarbonyl)-1,4-diazepane hydrochloride

Product 1

HCID 109620274-Amino-6-benzyloxy-7-methoxy-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinazolineYield 70%

Reagents, catalysts & solvents

1
HCID 2631-ButanolSolvent

Procedure

1-(4-Morpholinecarbonyl)-1,4-diazepane hydrochloride (16 g, 0.075 mol) and 4-amino-6-benzyloxy-2-chloro-7-methoxyquinazoline (15 g, 0.048 mol) were added to a solution of triethylamine (20 ml, 0.144 mol) in n-butanol (200 ml) and the reaction stirred at reflux for 1 hour. On cooling, the mixture was concentrated under reduced pressure and the residue partitioned between dichloromethane (400 ml) and water (400 ml). The phases were separated and the organic layer dried (MgSO4), filtered and evaporated under reduced pressure to give a cream coloured solid. Trituration with diethyl ether gave the title compound as a solid (16.35 g, 70%). Rf 0.50 (0.880 aqueous ammonia:methanol:dichloromethane 1:7:92, v/v). MS m/z 493 (MH)+. 1H-NMR (CDCl3): δ=2.03 (2H, m), 3.18 (4H, m), 3.34 (2H, t), 3.56 (2H, m), 3.65 (5H, m), 3.85 (2H, m), 4.00 (4H, m), 5.00 (1H, bs), 5.18 (2H, s), 6.87 (1H, bs), 7.37 (4H, m), 7.47 (3H, m).

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureOn cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customthe residue partitioned between dichloromethane (400 ml) and water (400 ml)
  5. customThe phases were separated
  6. dry with materialthe organic layer dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto give a cream

Sources & evidence

ORD record
ord-cc7be598e08b45c38a61dc494a64e083
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06048864

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes